[(acridine)BCl2]+: A borenium cation that is a strong boron- and carbon-based lewis acid

Ewan R. Clark, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

[(acridine)BCl2][AlCl4] was synthesized by halide abstraction from (acridine)BCl3 with AlCl3. The hydride ion affinity of the C9 position in [(acridine)BCl2]+ was calculated to be 14 kcal mol-1 greater than that at boron. [(acridine)BCl2][AlCl4] reacts with 1 equiv of acridine to form the strained boronium cation [(acridine)2BCl 2][AlCl4] and with P(mesityl)3 by photoinduced one-electron transfer to form the 9,9′-biacridane moiety by radical coupling. A stable frustrated Lewis pair (FLP) was formed on combining [(acridine)BCl2][AlCl4] and 2,4,6-tri-tert-butylpyridine (TBP), which heterolytically activated H2 at 100 C. The ultimate location of the hydride from H2 activation was the C9 position of acridine and not boron. Carbon Lewis acid based reactivity also occurred when thieno[3,2-b]thiophene was added to the [(acridine)BCl2][AlCl 4]/TBP FLP or to [(acridine)2BCl2][AlCl 4], with arylation of acridine at C9 observed for both.

Original languageEnglish
Pages (from-to)6712-6717
Number of pages6
JournalOrganometallics
Volume32
Issue number22
DOIs
Publication statusPublished - 25 Nov 2013

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